반응 #1077577

반응 방정식

L-2-hydroxyisocaproic acid

N,N-diisopropylethylamine

4,4-bis-(4-fluorophenyl)-butylamine

HBTU

→

desired product

수율 48.1%

(S)-2-Hydroxy-4-methyl-pentanoic acid [4,4-bis-(4-fluoro-phenyl)-butyl]-amide

수율 48.1%

용매

EtOAc

DMF

반응 조건

후처리

1. 1
   세척washed with saturated bicarbonate solution and brine
2. 2
   건조dried over Na2SO4
3. 3
   농축concentrated
4. 4
   기타The residue was chromatographed twice on silica gel
5. 5
   세척eluting with 2-4% MeOH/CH2Cl2

실험 절차

L-2-hydroxyisocaproic acid (102 mg, 0.77 mmol) was dissolved in DMF (5 mL) and treated with N,N-diisopropylethylamine (0.53 mL, 3.06 mmol), 4,4-bis-(4-fluorophenyl)-butylamine (200 mg, 0.77 mmol), and HBTU (292 mg, 0.77 mmol), then stirred overnight at room temperature. The reaction was diluted with EtOAc (125 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed twice on silica gel, eluting with 2-4% MeOH/CH2Cl2 to give 139 mg (48%) of the desired product as an oil. MS: 376.2 (M+1 for C22H27N1O2F2); an oil; TLC (SiO2), Rf 0.73 (8% MeOH/CH2Cl2); HPLC (7:3 CH3CN/H2O with 0.1% TFA, C-18 column) 96.46%, RT=5.448 min.

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